11 Surprising Celebrity Business Ventures

Actress-model. Writer-director. Singer-reality TV star. Hyphenates are standard business in the celebrity world. But not every boldface name-backed business venture is a natural extension of a star’s best-known talents. Here are 11 of the most surprising ones.

1. PAUL NEWMAN: CONDIMENT KING

Today, the late Paul Newman’s animated mug is as well known to supermarket shoppers as Aunt Jemima’s. But when the Oscar-winning actor launched his not-for-profit food company in 1982, it was met with a great big “WTF?” Sure, Cool Hand Luke could eat 50 hardboiled eggs in an hour, but concoct a vinaigrette with which to dress them? In the 31 years since its founding, and the five years since his passing, Newman’s “Let’s give it all away!” philosophy has generated more than $370 million in charitable donations—and one hell of a tasty Cobb salad!

2. MC HAMMER: SEARCH ENGINE KING

Anyone who can manage to make balloon pants look cool certainly has the power to take down Google ... right? In 2011, singer MC Hammer—he of “U Can’t Touch This” and “2 Legit 2 Quit” fame—announced his plans to launch WireDoo, an Internet search engine intended to compete with the likes of Google and Bing. Two years later, there’s still no WireDoo. You do the math (in technology years, of course).

3. KIM BASINGER: MAYOR OF BRASELTON

Kim Basinger had big plans for little Braselton, Georgia when she bought the tiny town (population: 500) for $20 million back in 1989 with an eye toward turning it into a tourist attraction. It didn’t happen. Five years later she was filing for bankruptcy and forced to sell the town … for a measly $1 million.

4. MARILYN MANSON: ABSINTHE CHEMIST

Rock stars launching liquor brands isn’t a brand-new idea (Sammy Hagar’s Cabo Wabo tequila has been thriving for years). But in the case of androgynous rocker Marilyn Manson, it’s the choice of spirit that is rather unusual: absinthe. In 2007, Manson partnered with Switzerland-based Lion Spirits to concoct a signature version of the green-colored, herb-based grain alcohol simply known as Mansinthe.

5. JEREMY RENNER: HOUSE FLIPPER

Before he was a two-time Oscar-nominated actor, Jeremy Renner was a struggling actor who needed to eke out a living away from the camera. So he turned to another passion: real estate. In the past decade, Renner and his business partner/fellow actor Kristoffer Winters have purchased, restored and resold more than a dozen homes with profits that dwarf some of the A-lister’s own paychecks. Like the $24.95 million Beverly Hills mansion that could net the duo a cool $18 million profit!

6. PATRICK DEMPSEY: BARISTA IN CHARGE

He may play a doctor on television, but in real life, Grey’s Anatomy star Patrick Dempsey is just a guy. One who spends his time racing expensive cars and taking on Starbucks to gain control of Tully’s, the 48-location Seattle-based coffee chain which declared bankruptcy last year. After six months of negotiations, the actor finally and officially took control of the company on July 1. No word yet on whether a McDreamy Macchiato is in the works.

7. STEVEN SODERBERGH: ONLINE ODDITY

Considering his tendency to direct two films per year, it’s amazing that filmmaker Steven Soderbergh even knows the meaning of “spare time.” But in May of this year, he launched Extension 765, a self-described “one-of-a-kind marketplace” where one can purchase art, booze, designer T-shirts and props in equal parts, all of which can be traced back to Soderbergh’s love of cinema in some way. (Even the site’s name is a reference to fellow moviemaker/entrepreneur Francis Ford Coppola’s The Conversation.)

8. NATALIE PORTMAN: VEGAN SHOEMAKER

In 2008, animal rights activist Natalie Portman proved that you don’t need to wear leather to look good when she launched a line of vegan footwear with New York City’s Te Casan boutique. Unfortunately, she also confirmed that a shoe doesn’t need to be made of leather to cost $325.

9. FRANCIS FORD COPPOLA: WINE MAKER

Forty years ago, Francis Ford Coppola’s name was synonymous with epic American cinema with movies like The Godfather, The Godfather: Part II, and Apocalypse Now (though definitely not The Godfather: Part III). While he’s still making movies today, Coppola is usually more likely to be found in a vineyard than on a film set. In 1975, the five-time Oscar winner used his paycheck from The Godfather to buy into the wine biz, where he’s been stomping up premium swill that pays tribute to his work (the Director’s Cut collection features a film strip label) and family (the Sofia collection is light and bubbly) for more than 35 years. His winery, in Geyersville, California, even features a Movie Gallery with props from his sets, including Don Corleone’s desk.

10. DONALD TRUMP: FOOTBALLER

Donald Trump has put his name on a lot of things: buildings, Websites, menswear, cologne, bottled water, vodka, steaks, and board games among them. But even The Donald’s endorsement couldn’t save the short-lived United States Football League, a professional spring football league that counted Herschel Walker, Doug Flutie, Jim Kelly and Steve Young among its stars. Trump’s insistence that the season be moved from spring to fall to compete with the NFL is often cited as the reason for the USFL’s untimely demise.

11. ANDREW SHUE: MOM BLOGGER

Andrew Shue became a television star as resident good guy Billy Campbell on Melrose Place, but he has also had a career as a professional soccer player (as part of the Zimbabwe Premier Soccer League, no less) and in 1993 he co-founded Do Something, a nonprofit organization dedicated to encouraging youngsters to make a difference. In 2006 he ventured into totally foreign territory when he (and another dude) started CafeMom, a social networking site for, yep, moms. It caught on quickly, becoming one of the Web’s most popular sites for women in no time, and in 2011 it was deemed a Top 50 Website by Time. See what happens when you stop letting Amanda Woodward push you around!

Jennifer M. Wood is a senior editor at MentalFloss.com, where she often writes about bad '80s movies, good British television, morbidly fascinating crimes, and Peeps. She writes more of the same for Condé Nast Traveler, Esquire, WIRED, Details, Rolling Stone, Complex and various other outlets.

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